Living (4.7 × 7.04)
Bay Window · hardwood floor · Combined W/Dining
Level: Main
29 Winchester St
Cabbagetown-South St. James Town, Toronto, Ontario M4X 1A6
Description
The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto's most storied neighbourhoods. With over 4200+ sq ft of living space (each unit is over 1000+ sq. ft in size), 29 Winchester offers a spacious and gracious living environment, complimented with multiple walk-out balconies, large windows, private decks and terraces, all overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and ensuite laundry in each unit. Parking is accessed via a private rear laneway (4 parking spaces at present including 1 tandem space, and the possibility to expand up to 6 car parking on site). Highly desirable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
01 / Property recordListing detailsFacts, history, rooms and location
Key Facts
- MLS® #
- C14111438
- Board
- TRREB MLS®
- Days on market
- Tax
- $12,354
- Size
- 3000-3500 sqft
- Lot
- 28.47 × 132.73 Feet
- Parking
- None, 4 Parking
Listing History
Listing activity for 29 Winchester St, Toronto, Ontario
| Date Start | Date End | List Price | Price | Event | Listing ID |
|---|---|---|---|---|---|
| N/A | N/A | $2,900,000 | N/A | For Sale | C14111438 |
Property Details
Property
- Property Type
- Fourplex
- Style
- 3-Storey
- Community
- Cabbagetown-South St. James Town
- Municipality
- Toronto
Inside
- Bedrooms
- 3+1
- Bathrooms
- 4
- Bathroom Detail
- 1, 4pc, Bsmt
- Bathroom Detail
- 1, 3pc, 2nd
- Bathroom Detail
- 1, 3pc, 3rd
- Bathroom Detail
- 1, 4pc, Main
- Basement Type
- Apartment
- Kitchens
- 3
Utilities
- Water
- Municipal
- Cooling
- Wall Unit
- Heating Type
- Baseboard
Building
- Size
- 3000-3500 sqft
- Construction
- Brick
Parking
- Driveway
- Lane, Private
- Garage Type
- None
- Add. Parking
- 4
- Total Parking
- 4
Land
- Sewer
- Sewers
- Lot Size
- 28.47 × 132.73 Feet
- Lot Size Code
- Feet
Additional
- Year built
- 100+
- Foundation
- Unknown
- Roof
- Asphalt Shingle, Metal
- Fireplace
- Y
- Pool
- None
- Den
- Y
- Family room
- Y
- Extras
- Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4 stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical(owned), HWT (rental), 4 fireplaces (as-is), 4x dishwashers). Full list of renovations / improvements included with attachments.
Rooms (15)
Kitchen (2.16 × 4.37)
Pass Through · Tile Floor · W/O To Balcony
Level: Main
Family (2.97 × 4.98)
hardwood floor · Window
Level: Main
Br (4.65 × 4.04)
Broadloom · Window · Double Closet
Level: Main
Living (4.65 × 7.09)
Laminate · Bay Window · Combined W/Dining
Level: 2nd
Kitchen (2.16 × 2.37)
Laminate · W/O To Balcony · Window
Level: 2nd
Family (2.97 × 4.98)
Laminate · Window · Pass Through
Level: 2nd
Br (2.95 × 4.01)
hardwood floor · Closet · Window
Level: 2nd
Living (3.91 × 5.05)
W/O To Terrace · hardwood floor · Combined W/Dining
Level: 3rd
Kitchen (1.68 × 4.75)
Laminate · Eat-In Kitchen · Window
Level: 3rd
Br (3.28 × 4.8)
Laminate · Window · Closet
Level: 3rd
Living (4.7 × 7.04)
Laminate · Window · Combined W/Dining
Level: Lower
Kitchen (2.13 × 3.96)
Open Concept · Window · Tile Floor
Level: Lower
Family (2.97 × 4.98)
W/O To Yard · Tile Floor
Level: Lower
Br (3.05 × 4.11)
Broadloom · Window · Closet
Level: Lower
Location
Land and environment
Public records about this location. Not part of the MLS® listing and not provided by the listing brokerage.
18 records read 10 on record nearby 8 checked, none on recordRead 2026-11-04
Water and conservation
- Not in Toronto and Region Conservation Authority’s mapped regulated area
- No mapped wetland within 120 m
- No water-supply well recorded within 250 m41 test or monitoring holes also recorded.
- Groundwater recorded about 12.4 m below ground nearbyThe middle water level in the well records within 500 m (180 records). It changes with the season and from spot to spot.
Toronto and Region Conservation Authority · Province of Ontario open data
Planning and building activity
- Outside the Greenbelt, Oak Ridges Moraine and Niagara Escarpment plan areas
- 69 building permits issued within 250 m in the last 2 years
- 2 open development applications within 250 mAn application is a proposal: it may change, be refused or never be built.
- Nearest airport: 3.9 km
- Mapped parcel: about 4,050 sq ftMeasured from the municipal parcel map, which can differ from the survey and from the lot size in the listing.
Province of Ontario open data · Municipal building permits · Municipal development applications · toronto.parcels
Around the home
- Nearest rail line: 940 m
- A trail on the Ontario trail network within 1 km
Province of Ontario open data
Environmental records
- No licensed pit or quarry within 2 km
- No recorded oil, gas or salt well within 250 m
- No facility within 1 km reports pollutant releases to Environment CanadaThe nearest is Enwave Energy Corporation — Walton Street Steam Plant, 1.5 km away. Only facilities above the inventory’s reporting thresholds are listed.
- No federal contaminated site within 1 kmThe federal inventory covers federal land only; it says nothing about provincial or private sites.
Province of Ontario open data · Government of Canada open data
Power and internet
- Electricity is distributed here by Toronto Hydro-Electric System Limited
- Wired internet 50/10 Mbps or faster is listed at this locationFixed wireless 50/10 Mbps or faster. LTE mobile coverage listed. ISED’s National Broadband Data at the nearest household point (10 m from the listing); 50/10 Mbps is its top category and includes faster plans. Confirm with a provider for this address.
- Across the surrounding area: fibre to the home, cable, DSL internet listedFibre to the home: Beanfield Metroconnect, Bell, CIK Telecom, Dotto One, FibreStream, Rally, Rogers. Cable: Rogers. DSL: Bell. Fixed wireless: Rogers, Routcom, SkyChoice Communications. Mobile: Bell, Freedom Mobile, Rogers, Telus. Satellite: Xplore. ISED’s list for the surrounding ~25 km² area; check with a provider for this address.
Ontario Energy Board · Innovation, Science and Economic Development Canada
None of this is an inspection of the property. Confirm anything that matters to you with the municipality, the conservation authority or the record’s publisher. Contains information licensed under the Open Government Licence – Canada. Contains information licensed under the Open Government Licence – Ontario. Contains information licensed under the Open Government Licence – Toronto. Contains information made available under the Toronto and Region Conservation Authority Open Data Licence v1.0.
02 / Plan your numbersToolsMortgage and cash-flow planning
Mortgage Tools
Mortgage calculator
20%
Monthly Payment
$13,294
- Down payment$580,000
- Mortgage amount$2,320,000
- Total interest$1,668,200
- Total cost$4,568,200
Cash flow analysis
$13,294
Total monthly payment
$14,323
Break-even down payment
100%
Cash flow-$14,323
03 / Community profileNeighbourhood demographicsPeople, homes and household context
Expand Neighbourhood demographics to load Statistics Canada census charts.
$2,900,000
$2,900,000
CAD
Estimate unavailable
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